Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides

While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated impro...

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Detalhes bibliográficos
Autores: García Pindado, Júlia, Willemse, Tom, Goss, Rebecca, Maes, Bert U. W., Giralt Lledó, Ernest, Ballet, Steven, Teixidó Turà, Meritxell
Tipo de documento: artigo
Estado:Versión aceptada para publicación
Data de publicação:2018
País:España
Recursos:Universidad de Barcelona
Repositório:Dipòsit Digital de la UB
OAI Identifier:oai:diposit.ub.edu:2445/121062
Acesso em linha:https://hdl.handle.net/2445/121062
Access Level:Acceso aberto
Palavra-chave:Pèptids
Triptòfan
Peptides
Tryptophan
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spelling Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptidesGarcía Pindado, JúliaWillemse, TomGoss, RebeccaMaes, Bert U. W.Giralt Lledó, ErnestBallet, StevenTeixidó Turà, MeritxellPèptidsTriptòfanPeptidesTryptophanWhile revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on‐resin Suzuki‐Miyaura cross‐coupling reactions.John Wiley & Sons2018info:eu-repo/semantics/articleinfo:eu-repo/semantics/acceptedVersionapplication/pdfhttps://hdl.handle.net/2445/121062Articles publicats en revistes (Química Inorgànica i Orgànica)reponame:Dipòsit Digital de la UBinstname:Universidad de BarcelonaInglésVersió postprint del document publicat a: http://dx.doi.org/10.1002/bip.23112Biopolymers, 2018http://dx.doi.org/10.1002/bip.23112(c) Wiley, 2018info:eu-repo/semantics/openAccessoai:diposit.ub.edu:2445/1210622026-05-27T06:46:51Z
dc.title.none.fl_str_mv Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
spellingShingle Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
García Pindado, Júlia
Pèptids
Triptòfan
Peptides
Tryptophan
title_short Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_full Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_fullStr Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_full_unstemmed Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
title_sort Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides
dc.creator.none.fl_str_mv García Pindado, Júlia
Willemse, Tom
Goss, Rebecca
Maes, Bert U. W.
Giralt Lledó, Ernest
Ballet, Steven
Teixidó Turà, Meritxell
author García Pindado, Júlia
author_facet García Pindado, Júlia
Willemse, Tom
Goss, Rebecca
Maes, Bert U. W.
Giralt Lledó, Ernest
Ballet, Steven
Teixidó Turà, Meritxell
author_role author
author2 Willemse, Tom
Goss, Rebecca
Maes, Bert U. W.
Giralt Lledó, Ernest
Ballet, Steven
Teixidó Turà, Meritxell
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Pèptids
Triptòfan
Peptides
Tryptophan
topic Pèptids
Triptòfan
Peptides
Tryptophan
description While revisiting biologically active natural peptides, the importance of the tryptophan residue became clear. In this article, the incorporation of this amino acid, brominated at different positions of the indole ring, into cyclic peptides was successfully achieved. These products demonstrated improved properties in terms of passive diffusion, permeability across membranes, biostability in human serum and cytotoxicity. Moreover, these brominated tryptophans at positions 5, 6, or 7 proved to be compatible as building blocks to prepare bicyclic stapled peptides by performing on‐resin Suzuki‐Miyaura cross‐coupling reactions.
publishDate 2018
dc.date.none.fl_str_mv 2018
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv https://hdl.handle.net/2445/121062
url https://hdl.handle.net/2445/121062
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv Versió postprint del document publicat a: http://dx.doi.org/10.1002/bip.23112
Biopolymers, 2018
http://dx.doi.org/10.1002/bip.23112
dc.rights.none.fl_str_mv (c) Wiley, 2018
info:eu-repo/semantics/openAccess
rights_invalid_str_mv (c) Wiley, 2018
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv John Wiley & Sons
publisher.none.fl_str_mv John Wiley & Sons
dc.source.none.fl_str_mv Articles publicats en revistes (Química Inorgànica i Orgànica)
reponame:Dipòsit Digital de la UB
instname:Universidad de Barcelona
instname_str Universidad de Barcelona
reponame_str Dipòsit Digital de la UB
collection Dipòsit Digital de la UB
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15.300724

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